Di-μ-chlorido-bis­[chlorido(1,10-phenanthroline-κ2N,N′)zinc(II)]

Yang, X.-M.; Leng, Q.-B.; Chen, Y.; He, Y.-G.; Luo, S.-W.

doi:10.1107/S1600536809014482

metal-organic compounds

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ISSN: 2056-9890

Volume 65| Part 5| May 2009| Page m567

doi:10.1107/S1600536809014482

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RETRACTED ARTICLE

This article has been retracted. To view the retraction notice, click here.

Retracted: Di-μ-chlorido-bis[chlorido(1,10-phenanthroline-κ²N,N′)zinc(II)]

Xiao-Mao Yang,^a ^* Qing-Bo Leng,^a Yi Chen,^a You-Gang He ^a and Shi-Wu Luo ^a

^aInstitute of Applied Materials, College of Resource & Environment Management, Jiangxi University of Finance and Economics, Nanchang 330013, People's Republic of China
^*Correspondence e-mail: xiaomaoyang09@126.com

(Received 12 April 2009; accepted 18 April 2009; online 25 April 2009)

In the crystal structure of the title complex, [Zn₂Cl₄(C₁₂H₈N₂)₂], each of the two five-coordinated Zn^II atoms displays a strongly distorted trigonal-bipyramidal geometry defined by two N atoms from the chelate ligand and by one terminal and two bridging chloride anions. The crystal structure is stabilized by C—H⋯Cl interactions. There is intermolecular π–π stacking between adjacent phenanthroline ligands, with a centroid–centroid distance of 3.151 (3) Å.

Related literature

For the use of metal complexes of phenanthroline and its derivatives with π-π stacking to study the hydrolysis of biologically important phosphate diesters with poor leaving groups, see: Wall et al. (1999 ). For the structures of a series of metal complexes, see: Wu et al. (2003 ); Pan & Xu (2004 ); Li et al. (2005 ). For bond-length data, see: Allen et al. (1987 ).

Experimental

Crystal data

[Zn₂Cl₄(C₁₂H₈N₂)₂]
M_r = 632.95
Monoclinic, C c
a = 9.8537 (12) Å
b = 17.873 (2) Å
c = 13.3798 (12) Å
β = 106.502 (3)°
V = 2259.3 (4) Å³
Z = 4
Mo Kα radiation
μ = 2.62 mm⁻¹
T = 293 K
0.19 × 0.16 × 0.12 mm

Data collection

Bruker APEXII area-detector diffractometer
Absorption correction: multi-scan (SADABS; Bruker, 2000 ) T_min = 0.636, T_max = 0.744
7229 measured reflections
4218 independent reflections
3453 reflections with I > 2σ(I)
R_int = 0.033

Refinement

R[F² > 2σ(F²)] = 0.033
wR(F²) = 0.073
S = 1.00
4218 reflections
307 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.47 e Å⁻³
Δρ_min = −0.43 e Å⁻³
Absolute structure: Flack (1983 ), 1983 Friedel pairs
Flack parameter: 0.079 (12)

Table 1
Selected geometric parameters (Å, °)

Zn1—Cl1	2.2629 (16)
Zn1—Cl2	2.2596 (15)
Zn1—Cl3	2.7049 (14)
Zn1—N1	2.041 (4)
Zn1—N2	2.046 (4)
Zn2—Cl2	2.8525 (15)
Zn2—Cl3	2.2839 (14)
Zn2—Cl4	2.2545 (14)
Zn2—N3	2.031 (4)
Zn2—N4	2.032 (4)

Table 2
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cl1	0.93	2.68	3.229 (7)	118
C6—H6⋯Cl2ⁱ	0.93	2.77	3.525 (6)	139
C10—H10⋯Cl2	0.93	2.68	3.235 (6)	119
C13—H13⋯Cl3	0.93	2.62	3.200 (6)	121
C17—H17⋯Cl3ⁱⁱ	0.93	2.67	3.500 (7)	149
C18—H18⋯Cl4ⁱⁱ	0.93	2.82	3.742 (7)	173
C22—H22⋯Cl4	0.93	2.68	3.238 (6)	119
Symmetry codes: (i) $[x-{\script{1\over 2}}, y+{\script{1\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y-{\script{1\over 2}}, z]$ .

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT; program(s) used to solve structure: SHELXTL (Sheldrick, 2008 ); program(s) used to refine structure: SHELXTL; molecular graphics: SHELXTL; software used to prepare material for publication: SHELXTL.

Supporting information

Crystal structure: contains datablocks I, global. DOI: 10.1107/S1600536809014482/at2764sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809014482/at2764Isup2.hkl

checkCIF report

Comment top

Simple metal complexes of phenanthroline and its derivatives with π-π stacking have attracted great interest because they can be used to study the hydrolysis of biologically important phosphate diesters with poor leaving groups (Wall et al., 1999). A series of metal complexes incorporating different aromatic ligands such as phenanthroline(phen), benzimidazole and quinoline have been prepared and their crystal structures provide useful information about π-π stacking (Wu et al., 2003; Pan & Xu, 2004; Li et al., 2005). We report herein the crystal structure of the title compound, (I).

In the molecule of (I) (Fig. 1), the ligand bond lengths and angles are within normal ranges (Allen et al., 1987). In the crystal structure of the title complex, each of the two five-coordinated Zn^II atoms displays a strongly distorted trigonalbipyramidal geometry, defined by two N atom from the organic ligand, and by one terminal and two bridging chloride anions (Table 1).

The crystal structure is stabilized by C—H···Cl interactions (Table 1). There is intermolecular π-π stacking between adjacent phenanthrolines, with a centroid-centroid distance of 3.151 (3) Å (symmetry code: -1/2 + x, 1/2 + y, z). These π-π stacking interactions lead to a supramolecular network structure (Fig. 2).

Related literature top

For the use of metal complexes of phenanthroline and its derivatives with π-π stacking to study the hydrolysis of biologically important phosphate diesters with poor leaving groups, see: Wall et al. (1999). For the structures of a series of metal complexes, see: Wu et al. (2003); Pan & Xu (2004); Li et al. (2005). For bond-length data, see: Allen et al. (1987).

Experimental top

Crystals of the title compound were synthesized using hydrothermal method in a 23 ml Teflon-lined Parr bomb, which was then sealed. Zinc(II) chloride (136.3 mg, 1 mmol), phen (396 mg, 2 mmol) and distilled water (10 g) were placed into the bomb and sealed. The bomb was then heated under autogenous pressure up to 453 K over the course of 7 d and allowed to cool at room temperature for 24 h. Upon opening the bomb, a clear colourless solution was decanted from small colourless crystals. These crystals were washed with distilled water followed by ethanol, and allowed to air-dry at room temperature.

Computing details top

Data collection: SMART (Bruker, 2000); cell refinement: SAINT (Bruker, 2000); data reduction: SAINT (Bruker, 2000); program(s) used to solve structure: SHELXTL (Sheldrick, 2008); program(s) used to refine structure: SHELXTL (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL (Sheldrick, 2008).

Figures top

	Fig. 1. The molecular structure of the title complex, with the atom-numbering scheme. Displacement ellipsoids are drawn at the 30% probability level.
	Fig. 2. A packing diagram of (I). Hydrogen bonds are shown as dashed lines.

Di-µ-chlorido-bis[chlorido(1,10-phenanthroline- κ²N,N')zinc(II)] top

Crystal data top

[Zn₂Cl₄(C₁₂H₈N₂)₂]	F(000) = 1264
M_r = 632.95	D_x = 1.861 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 3822 reflections
a = 9.8537 (12) Å	θ = 2.3–27.3°
b = 17.873 (2) Å	µ = 2.62 mm⁻¹
c = 13.3798 (12) Å	T = 293 K
β = 106.502 (3)°	Plane, colourless
V = 2259.3 (4) Å³	0.19 × 0.16 × 0.12 mm
Z = 4

Data collection top

Bruker APEXII area-detector diffractometer	4218 independent reflections
Radiation source: fine-focus sealed tube	3453 reflections with I > 2σ(I)
Graphite monochromator	R_int = 0.033
ϕ and ω scans	θ_max = 26.0°, θ_min = 2.3°
Absorption correction: multi-scan (SADABS; Bruker, 2000))	h = −12→11
T_min = 0.636, T_max = 0.744	k = −22→21
7229 measured reflections	l = −16→16

Refinement top

Refinement on F²	Secondary atom site location: difference Fourier map
Least-squares matrix: full	Hydrogen site location: inferred from neighbouring sites
R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.073	w = 1/[σ²(F_o²) + (0.03P)² + 0.16P] where P = (F_o² + 2F_c²)/3
S = 1.00	(Δ/σ)_max < 0.001
4218 reflections	Δρ_max = 0.47 e Å⁻³
307 parameters	Δρ_min = −0.43 e Å⁻³
2 restraints	Absolute structure: Flack (1983), 1983 Freidel pairs
Primary atom site location: structure-invariant direct methods	Absolute structure parameter: 0.079 (12)

Crystal data top

[Zn₂Cl₄(C₁₂H₈N₂)₂]	V = 2259.3 (4) Å³
M_r = 632.95	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 9.8537 (12) Å	µ = 2.62 mm⁻¹
b = 17.873 (2) Å	T = 293 K
c = 13.3798 (12) Å	0.19 × 0.16 × 0.12 mm
β = 106.502 (3)°

Data collection top

Bruker APEXII area-detector diffractometer	4218 independent reflections
Absorption correction: multi-scan (SADABS; Bruker, 2000))	3453 reflections with I > 2σ(I)
T_min = 0.636, T_max = 0.744	R_int = 0.033
7229 measured reflections

Refinement top

R[F² > 2σ(F²)] = 0.033	H-atom parameters constrained
wR(F²) = 0.073	Δρ_max = 0.47 e Å⁻³
S = 1.00	Δρ_min = −0.43 e Å⁻³
4218 reflections	Absolute structure: Flack (1983), 1983 Freidel pairs
307 parameters	Absolute structure parameter: 0.079 (12)
2 restraints

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
Zn1	0.69851 (5)	0.33467 (3)	0.27140 (4)	0.03385 (16)
Zn2	0.99585 (6)	0.30433 (3)	0.49316 (5)	0.03673 (16)
Cl3	0.76987 (13)	0.34082 (7)	0.48194 (10)	0.0360 (3)
Cl2	0.91611 (14)	0.29488 (8)	0.27124 (10)	0.0366 (4)
Cl1	0.60068 (15)	0.21961 (8)	0.23650 (12)	0.0457 (4)
Cl4	1.08005 (15)	0.42235 (7)	0.50920 (12)	0.0478 (4)
N1	0.5066 (4)	0.3839 (2)	0.2553 (3)	0.0315 (10)
N2	0.7513 (4)	0.4444 (2)	0.2596 (3)	0.0321 (10)
C11	0.6385 (5)	0.4924 (3)	0.2474 (3)	0.0277 (11)
C12	0.5088 (5)	0.4583 (3)	0.2469 (4)	0.0303 (12)
C1	0.3845 (6)	0.3509 (4)	0.2559 (4)	0.0489 (16)
H1	0.3828	0.2993	0.2635	0.059*
C2	0.2584 (6)	0.3918 (4)	0.2455 (5)	0.0515 (16)
H2	0.1752	0.3675	0.2461	0.062*
C8	0.7830 (7)	0.5967 (3)	0.2373 (4)	0.0468 (16)
H8	0.7944	0.6476	0.2278	0.056*
C7	0.6504 (6)	0.5691 (3)	0.2363 (4)	0.0367 (13)
C10	0.8756 (6)	0.4746 (3)	0.2632 (4)	0.0366 (12)
H10	0.9538	0.4433	0.2739	0.044*
C3	0.2615 (6)	0.4669 (4)	0.2345 (4)	0.0495 (15)
H3	0.1788	0.4943	0.2266	0.059*
C4	0.3884 (6)	0.5051 (3)	0.2347 (4)	0.0401 (14)
C6	0.5230 (6)	0.6132 (3)	0.2241 (4)	0.0447 (14)
H6	0.5271	0.6646	0.2145	0.054*
C5	0.4016 (7)	0.5830 (3)	0.2260 (4)	0.0497 (16)
H5	0.3238	0.6136	0.2215	0.060*
N4	0.9434 (4)	0.1943 (2)	0.4907 (3)	0.0284 (9)
N3	1.1864 (4)	0.2591 (2)	0.4971 (3)	0.0357 (10)
C13	0.8177 (6)	0.1637 (3)	0.4836 (4)	0.0408 (13)
H13	0.7405	0.1948	0.4789	0.049*
C23	1.1830 (5)	0.1816 (3)	0.4989 (4)	0.0342 (13)
C22	1.3047 (6)	0.2925 (3)	0.4985 (4)	0.0403 (15)
H22	1.3085	0.3445	0.4992	0.048*
C24	1.0533 (6)	0.1489 (3)	0.4961 (4)	0.0309 (12)
C16	1.0413 (7)	0.0691 (3)	0.4961 (4)	0.0429 (15)
C17	1.1629 (7)	0.0258 (4)	0.5004 (4)	0.0515 (17)
H17	1.1565	−0.0261	0.5016	0.062*
C15	0.9031 (7)	0.0404 (3)	0.4884 (4)	0.0477 (15)
H15	0.8885	−0.0110	0.4873	0.057*
C18	1.2876 (7)	0.0575 (4)	0.5027 (4)	0.0545 (18)
H18	1.3657	0.0274	0.5057	0.065*
C14	0.7984 (7)	0.0854 (3)	0.4831 (4)	0.0428 (15)
H14	0.7094	0.0660	0.4788	0.051*
C19	1.3008 (6)	0.1378 (3)	0.5006 (4)	0.0450 (15)
C20	1.4266 (7)	0.1761 (4)	0.5006 (5)	0.063 (2)
H20	1.5086	0.1500	0.5016	0.075*
C21	1.4242 (7)	0.2522 (5)	0.4989 (5)	0.0599 (19)
H21	1.5059	0.2779	0.4980	0.072*
C9	0.8946 (7)	0.5507 (3)	0.2517 (5)	0.0473 (16)
H9	0.9834	0.5695	0.2540	0.057*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
Zn1	0.0277 (3)	0.0256 (3)	0.0473 (3)	0.0018 (3)	0.0090 (2)	0.0012 (3)
Zn2	0.0278 (3)	0.0222 (3)	0.0593 (4)	0.0017 (3)	0.0111 (3)	−0.0001 (3)
Cl3	0.0305 (8)	0.0301 (7)	0.0480 (8)	0.0072 (5)	0.0121 (6)	−0.0017 (6)
Cl2	0.0308 (8)	0.0313 (8)	0.0493 (8)	0.0074 (6)	0.0141 (6)	−0.0001 (6)
Cl1	0.0413 (9)	0.0267 (8)	0.0675 (10)	−0.0035 (7)	0.0127 (7)	−0.0038 (7)
Cl4	0.0398 (8)	0.0239 (7)	0.0723 (10)	−0.0047 (6)	0.0037 (7)	0.0008 (6)
N1	0.025 (3)	0.033 (3)	0.036 (2)	0.0032 (19)	0.0084 (18)	−0.0008 (18)
N2	0.029 (2)	0.027 (2)	0.042 (2)	0.009 (2)	0.0108 (18)	0.0046 (18)
C11	0.030 (3)	0.022 (3)	0.030 (2)	0.002 (2)	0.006 (2)	0.0006 (19)
C12	0.029 (3)	0.029 (3)	0.032 (3)	0.009 (2)	0.006 (2)	−0.003 (2)
C1	0.047 (4)	0.043 (4)	0.058 (4)	0.000 (3)	0.016 (3)	0.007 (3)
C2	0.026 (3)	0.066 (5)	0.065 (4)	0.004 (3)	0.016 (3)	0.004 (3)
C8	0.067 (5)	0.020 (3)	0.049 (3)	−0.008 (3)	0.010 (3)	−0.002 (2)
C7	0.048 (3)	0.022 (3)	0.038 (3)	0.012 (2)	0.008 (2)	0.001 (2)
C10	0.029 (3)	0.027 (3)	0.052 (3)	0.002 (2)	0.009 (2)	0.003 (2)
C3	0.033 (3)	0.060 (4)	0.056 (4)	0.016 (3)	0.013 (3)	0.002 (3)
C4	0.031 (3)	0.049 (4)	0.039 (3)	0.014 (3)	0.008 (2)	−0.002 (3)
C6	0.062 (4)	0.028 (3)	0.042 (3)	0.016 (3)	0.011 (3)	0.005 (2)
C5	0.045 (4)	0.047 (4)	0.056 (4)	0.027 (3)	0.011 (3)	−0.002 (3)
N4	0.025 (2)	0.021 (2)	0.040 (2)	−0.0010 (18)	0.0112 (17)	0.0033 (17)
N3	0.030 (3)	0.034 (3)	0.042 (2)	0.007 (2)	0.0083 (19)	0.0000 (19)
C13	0.031 (3)	0.034 (3)	0.054 (3)	−0.004 (3)	0.007 (2)	0.009 (3)
C23	0.034 (3)	0.039 (4)	0.029 (3)	0.010 (2)	0.007 (2)	0.001 (2)
C22	0.021 (3)	0.049 (4)	0.052 (4)	−0.009 (3)	0.011 (2)	0.000 (3)
C24	0.038 (3)	0.022 (3)	0.033 (3)	0.010 (2)	0.010 (2)	0.001 (2)
C16	0.071 (4)	0.025 (3)	0.032 (3)	0.012 (3)	0.013 (3)	0.002 (2)
C17	0.081 (5)	0.037 (3)	0.036 (3)	0.027 (4)	0.016 (3)	−0.001 (2)
C15	0.073 (5)	0.021 (3)	0.049 (3)	−0.008 (3)	0.016 (3)	−0.004 (2)
C18	0.066 (5)	0.047 (4)	0.050 (4)	0.032 (4)	0.015 (3)	0.004 (3)
C14	0.047 (4)	0.021 (3)	0.059 (4)	−0.008 (3)	0.012 (3)	0.002 (2)
C19	0.045 (4)	0.054 (4)	0.034 (3)	0.025 (3)	0.009 (2)	0.005 (3)
C20	0.031 (3)	0.098 (6)	0.059 (4)	0.019 (4)	0.012 (3)	−0.010 (4)
C21	0.022 (3)	0.085 (6)	0.074 (5)	0.000 (4)	0.015 (3)	0.001 (4)
C9	0.042 (4)	0.031 (3)	0.070 (4)	−0.007 (3)	0.017 (3)	0.007 (3)

Geometric parameters (Å, º) top

Zn1—Cl1	2.2629 (16)	C4—C5	1.406 (8)
Zn1—Cl2	2.2596 (15)	C6—C5	1.318 (8)
Zn1—Cl3	2.7049 (14)	C6—H6	0.9300
Zn1—N1	2.041 (4)	C5—H5	0.9300
Zn1—N2	2.046 (4)	N4—C13	1.332 (6)
Zn2—Cl2	2.8525 (15)	N4—C24	1.338 (6)
Zn2—Cl3	2.2839 (14)	N3—C22	1.305 (7)
Zn2—Cl4	2.2545 (14)	N3—C23	1.387 (7)
Zn2—N3	2.031 (4)	C13—C14	1.412 (7)
Zn2—N4	2.032 (4)	C13—H13	0.9300
N1—C12	1.335 (6)	C23—C19	1.395 (7)
N1—C1	1.341 (7)	C23—C24	1.397 (7)
N2—C10	1.328 (6)	C22—C21	1.380 (9)
N2—C11	1.376 (6)	C22—H22	0.9300
C11—C7	1.388 (7)	C24—C16	1.431 (7)
C11—C12	1.414 (7)	C16—C17	1.413 (7)
C12—C4	1.423 (7)	C16—C15	1.431 (8)
C1—C2	1.413 (8)	C17—C18	1.345 (8)
C1—H1	0.9300	C17—H17	0.9300
C2—C3	1.353 (8)	C15—C14	1.294 (9)
C2—H2	0.9300	C15—H15	0.9300
C8—C9	1.342 (8)	C18—C19	1.443 (9)
C8—C7	1.393 (8)	C18—H18	0.9300
C8—H8	0.9300	C14—H14	0.9300
C7—C6	1.452 (7)	C19—C20	1.416 (9)
C10—C9	1.386 (8)	C20—C21	1.359 (10)
C10—H10	0.9300	C20—H20	0.9300
C3—C4	1.424 (8)	C21—H21	0.9300
C3—H3	0.9300	C9—H9	0.9300

Cl1—Zn1—Cl2	93.58 (6)	C5—C6—H6	118.8
Cl1—Zn1—Cl3	102.79 (5)	C7—C6—H6	118.8
Cl2—Zn1—Cl3	92.74 (5)	C6—C5—C4	120.8 (5)
N1—Zn1—Cl1	92.42 (13)	C6—C5—H5	119.6
N2—Zn1—Cl1	163.25 (11)	C4—C5—H5	119.6
N1—Zn1—Cl2	170.64 (13)	C13—N4—C24	118.5 (5)
N2—Zn1—Cl2	92.27 (12)	C13—N4—Zn2	128.7 (4)
N1—Zn1—Cl3	92.93 (11)	C24—N4—Zn2	112.8 (3)
N2—Zn1—Cl3	92.59 (11)	C22—N3—C23	118.8 (5)
N1—Zn1—N2	80.04 (17)	C22—N3—Zn2	129.3 (4)
Cl3—Zn2—Cl4	93.71 (6)	C23—N3—Zn2	111.8 (3)
N3—Zn2—Cl3	172.83 (13)	N4—C13—C14	121.8 (5)
N4—Zn2—Cl3	92.09 (12)	N4—C13—H13	119.1
N3—Zn2—Cl4	93.28 (14)	C14—C13—H13	119.1
N4—Zn2—Cl4	172.95 (12)	N3—C23—C19	122.5 (5)
N3—Zn2—N4	81.04 (16)	N3—C23—C24	116.4 (4)
Zn2—Cl3—Zn1	90.98 (4)	C19—C23—C24	121.1 (5)
C12—N1—C1	118.3 (5)	N3—C22—C21	121.3 (6)
C12—N1—Zn1	113.6 (3)	N3—C22—H22	119.4
C1—N1—Zn1	128.0 (4)	C21—C22—H22	119.4
C10—N2—C11	117.2 (4)	N4—C24—C23	117.9 (4)
C10—N2—Zn1	129.8 (4)	N4—C24—C16	122.6 (5)
C11—N2—Zn1	113.1 (3)	C23—C24—C16	119.4 (5)
N2—C11—C7	122.6 (5)	C17—C16—C15	125.8 (5)
N2—C11—C12	115.5 (4)	C17—C16—C24	118.5 (6)
C7—C11—C12	122.0 (5)	C15—C16—C24	115.7 (5)
N1—C12—C11	117.7 (4)	C18—C17—C16	121.9 (6)
N1—C12—C4	124.2 (5)	C18—C17—H17	119.1
C11—C12—C4	118.0 (5)	C16—C17—H17	119.1
N1—C1—C2	122.5 (6)	C14—C15—C16	120.6 (5)
N1—C1—H1	118.8	C14—C15—H15	119.7
C2—C1—H1	118.8	C16—C15—H15	119.7
C3—C2—C1	118.5 (6)	C17—C18—C19	120.4 (6)
C3—C2—H2	120.7	C17—C18—H18	119.8
C1—C2—H2	120.7	C19—C18—H18	119.8
C9—C8—C7	120.8 (5)	C15—C14—C13	120.8 (6)
C9—C8—H8	119.6	C15—C14—H14	119.6
C7—C8—H8	119.6	C13—C14—H14	119.6
C11—C7—C8	117.2 (5)	C23—C19—C20	117.0 (6)
C11—C7—C6	116.8 (5)	C23—C19—C18	118.6 (6)
C8—C7—C6	126.0 (5)	C20—C19—C18	124.4 (6)
N2—C10—C9	123.2 (5)	C21—C20—C19	118.2 (6)
N2—C10—H10	118.4	C21—C20—H20	120.9
C9—C10—H10	118.4	C19—C20—H20	120.9
C2—C3—C4	121.5 (5)	C20—C21—C22	122.2 (7)
C2—C3—H3	119.3	C20—C21—H21	118.9
C4—C3—H3	119.3	C22—C21—H21	118.9
C5—C4—C12	119.9 (5)	C8—C9—C10	119.1 (6)
C5—C4—C3	125.2 (5)	C8—C9—H9	120.5
C12—C4—C3	114.9 (5)	C10—C9—H9	120.5
C5—C6—C7	122.4 (5)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.68	3.229 (7)	118
C6—H6···Cl2ⁱ	0.93	2.77	3.525 (6)	139
C10—H10···Cl2	0.93	2.68	3.235 (6)	119
C13—H13···Cl3	0.93	2.62	3.200 (6)	121
C17—H17···Cl3ⁱⁱ	0.93	2.67	3.500 (7)	149
C18—H18···Cl4ⁱⁱ	0.93	2.82	3.742 (7)	173
C22—H22···Cl4	0.93	2.68	3.238 (6)	119

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, y−1/2, z.

Experimental details

Crystal data
Chemical formula	[Zn₂Cl₄(C₁₂H₈N₂)₂]
M_r	632.95
Crystal system, space group	Monoclinic, Cc
Temperature (K)	293
a, b, c (Å)	9.8537 (12), 17.873 (2), 13.3798 (12)
β (°)	106.502 (3)
V (Å³)	2259.3 (4)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	2.62
Crystal size (mm)	0.19 × 0.16 × 0.12

Data collection
Diffractometer	Bruker APEXII area-detector diffractometer
Absorption correction	Multi-scan (SADABS; Bruker, 2000))
T_min, T_max	0.636, 0.744
No. of measured, independent and observed [I > 2σ(I)] reflections	7229, 4218, 3453
R_int	0.033
(sin θ/λ)_max (Å⁻¹)	0.617

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.033, 0.073, 1.00
No. of reflections	4218
No. of parameters	307
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.47, −0.43
Absolute structure	Flack (1983), 1983 Freidel pairs
Absolute structure parameter	0.079 (12)

Computer programs: SMART (Bruker, 2000), SAINT (Bruker, 2000), SHELXTL (Sheldrick, 2008).

Selected geometric parameters (Å, º) top

Zn1—Cl1	2.2629 (16)	Zn2—Cl2	2.8525 (15)
Zn1—Cl2	2.2596 (15)	Zn2—Cl3	2.2839 (14)
Zn1—Cl3	2.7049 (14)	Zn2—Cl4	2.2545 (14)
Zn1—N1	2.041 (4)	Zn2—N3	2.031 (4)
Zn1—N2	2.046 (4)	Zn2—N4	2.032 (4)

Cl1—Zn1—Cl2	93.58 (6)	N2—Zn1—Cl3	92.59 (11)
Cl1—Zn1—Cl3	102.79 (5)	N1—Zn1—N2	80.04 (17)
Cl2—Zn1—Cl3	92.74 (5)	Cl3—Zn2—Cl4	93.71 (6)
N1—Zn1—Cl1	92.42 (13)	N3—Zn2—Cl3	172.83 (13)
N2—Zn1—Cl1	163.25 (11)	N4—Zn2—Cl3	92.09 (12)
N1—Zn1—Cl2	170.64 (13)	N3—Zn2—Cl4	93.28 (14)
N2—Zn1—Cl2	92.27 (12)	N4—Zn2—Cl4	172.95 (12)
N1—Zn1—Cl3	92.93 (11)	N3—Zn2—N4	81.04 (16)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cl1	0.93	2.68	3.229 (7)	118
C6—H6···Cl2ⁱ	0.93	2.77	3.525 (6)	139
C10—H10···Cl2	0.93	2.68	3.235 (6)	119
C13—H13···Cl3	0.93	2.62	3.200 (6)	121
C17—H17···Cl3ⁱⁱ	0.93	2.67	3.500 (7)	149
C18—H18···Cl4ⁱⁱ	0.93	2.82	3.742 (7)	173
C22—H22···Cl4	0.93	2.68	3.238 (6)	119

Symmetry codes: (i) x−1/2, y+1/2, z; (ii) x+1/2, y−1/2, z.

Acknowledgements

We thank the Youth Program of Jiangxi University of Finance and Economics for financial support of this work.

References

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